(2R,5S,6S)-6-methyl-2-phenyl-1-aza-3-oxabicyclo[3.3.0]octan-8-one

Base Information

• Chemical Name: (2R,5S,6S)-6-methyl-2-phenyl-1-aza-3-oxabicyclo[3.3.0]octan-8-one
• CAS No.: 362660-19-3
• Molecular Formula: C₁₃H₁₅NO₂
• Molecular Weight: 217.268
• Mol file: 362660-19-3.mol

Synonyms:(2R,5S,6S)-6-methyl-2-phenyl-1-aza-3-oxabicyclo[3.3.0]octan-8-one

Chemical Property of (2R,5S,6S)-6-methyl-2-phenyl-1-aza-3-oxabicyclo[3.3.0]octan-8-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5S,6S)-6-methyl-2-phenyl-1-aza-3-oxabicyclo[3.3.0]octan-8-one

There total 2 articles about (2R,5S,6S)-6-methyl-2-phenyl-1-aza-3-oxabicyclo[3.3.0]octan-8-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

methyllithium (917-54-4) + (3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one (134107-65-6) → (2R,5S,6S)-6-methyl-2-phenyl-1-aza-3-oxabicyclo[3.3.0]octan-8-one (362660-19-3)

Guidance literature:

methyllithium; With copper(l) iodide; In tetrahydrofuran; at 0 ℃; for 0.5h;

(3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one; With chloro-trimethyl-silane; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1016/S0957-4166(01)00231-2

Reference yield:

(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one (103201-79-2,1820583-17-2) → (2R,5S,6S)-6-methyl-2-phenyl-1-aza-3-oxabicyclo[3.3.0]octan-8-one (362660-19-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / diisopropylamine; n-BuLi; N-tert-butyl benzenesulfinimidoyl chloride / tetrahydrofuran; hexane / -78 - -10 °C

2: 86 percent / CuI; Me₃SiCl / tetrahydrofuran; diethyl ether / 1 h / -78 °C

With copper(l) iodide; n-butyllithium; chloro-trimethyl-silane; N-tert-butyl benzenesulfinimidoyl chloride; diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; 2: Michael reaction;

DOI:10.1016/j.tet.2004.06.111

Reference yield: 96.0%

(2R,5S,6S)-6-methyl-2-phenyl-1-aza-3-oxabicyclo[3.3.0]octan-8-one (362660-19-3) + methyl iodide (74-88-4) → (2R,5S,6S,7S)-6,7-dimethyl-2-phenyl-1-aza-3-oxabicyclo[3.3.0]octan-8-one (362660-20-6)

Guidance literature:

(2R,5S,6S)-6-methyl-2-phenyl-1-aza-3-oxabicyclo[3.3.0]octan-8-one; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

methyl iodide; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1016/S0957-4166(01)00231-2

upstream raw materials:

methyllithium

(3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one

(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

Downstream raw materials:

(2R,5S,6S,7S)-6,7-dimethyl-2-phenyl-1-aza-3-oxabicyclo[3.3.0]octan-8-one

(2S,3S)-3-methyl-5-oxopyrrolidine-2-carboxylic benzoic anhydride

(2S,3S)-3-methyl-5-oxopyrrolidine-2-carboxylic acid benzyl ester

(2S,3S)-3-methyl-5-oxopyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester